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The Six Cheapest Places to Fly This Winter

With a brand new year comes a brand new calendar full of potential vacation days. For those eager to begin 2022 with a little travel —preferably at an equally small price—the sleepy stretch of winter that follows the holidays is one of the best times to go. Not only are crowds at a minimum, but you’ll typically find some of the lowest fares of the year available before the spring rush of late March. However, airlines are still operating at reduced fleets which will impact fares along many routes and can make deals tough to find. So where will you spend your winter break in 2022? We’ve found six incredibly cheap places to fly this winter.

Flights to San Juan, Puerto Rico (SJU)

San Juan, Puerto Rico Caribbean coast along Paseo de la Princesa
SeanPavonePhoto | Adobe Stock

For a fuss-free winter getaway at the last minute, San Juan is a hard one to beat. Not only is this year-round paradise relatively easy to reach from much of the U.S., but, as a U.S. territory, your visit won’t require a passport or even a change of currency. Most importantly, for budget travelers, flights to Puerto Rico are inexpensive. Flights can be had for under $280 round-trip, nonstop, on legacy carriers from major East Coast Cities. If departing from the West Coast, you can expect to pay around $330 for the cheapest flight, and, yes, that will involve a connection. If you’re willing to travel light on low-cost carriers like Spirit or Frontier, you’ll pay even less, but only if you adhere to the bare-bones carry-on policies required of their lowest fares. 

Sound good? Here’s a look at current fares to San Juan (SJU) from your area.   

Flights to Los Angeles (LAX)

Busy highway in Los Angeles, California
blvdone | Adobe Stock

A long weekend of reliable sunshine, swimming pools, and excellent tacos are sometimes all you need to break through a seasonal funk. L.A. has plenty of all three and is the gateway to other SoCal attractions like Disneyland and nearby Palm Springs and Joshua Tree. No matter where in the U.S. you’re departing from, a cheap winter flight to LAX will generally cost you around $300 off-peak this winter, give or take $30. 

See our latest low fares to Los Angeles (LAX) from your nearest airport. 

Flights to London (LHR)

The Palace of Westminster and Westminster Bridge in London
Leonid Andronov | Adobe Stock

After two years of fluctuating restrictions, including an all-out ban and lengthy quarantine period, uncomplicated travel to London is once again a possibility for Americans. London may seem out of place on this list but fares for mid-week winter travel have been consistently reasonable from numerous U.S. cities. Vaccinated Americans can travel to the U.K. without a COVID-19 test but must submit to a test by day two of their visit. Unvaccinated Americans can also travel to the U.K. However, they must pre-book a series of two tests to be taken during a mandatory 10-day quarantine. As far as affordability, fares to London may not be as low as they were during the low-cost heyday of the 2010s, but they aren’t unreasonable either. For example, New Yorkers can hop a flight to Heathrow for $339 round-trip, currently on Portugal’s TAP Air. The lowest fare will generally run you around $500 round-trip from elsewhere on the East Coast or in the Midwest. From West Coast cities, that figure jumps by about $60. But, again, that’s on the low-end for midweek travel. 

Have a look at current deals to London (LHR) from your nearest airport. 

Flights to San Jose (SJO), Costa Rica

Church in San Jose, Costa Rica
Gian | Adobe Stock

Costa Rica may not be the cheapest destination in Central America but, for travelers willing to pay a tad more at the tail end of a pandemic, this ecotourism hotspot offers reliable tourism infrastructure at a value. Flights to San Jose are reasonable from both coasts. New Yorkers can snag a nonstop on JetBlue this February for $185 round-trip, while Angelenos can find similarly priced flights on low-cost carrier Volaris. Elsewhere the lowest average fare hovers around $300 round-trip, plus or minus $40. 

Check out our recent low fares to San Jose (SJO) from your closest airport.  

Flights to Florida

Skyline of Orlando, Florida
aiisha | Adobe Stock

When the decision fatigue sets in and you feel incapable of choosing a sunny winter getaway, the right choice is sometimes the most obvious. Visitors to Florida will find plenty of coastline to go around, reasonably-priced accommodations for every budget, and more than enough flights to transport you cheaply to one of the three big local airports in Miami, Ft. Lauderdale, or West Palm Beach. In Orlando (MCO), Disneyheads can just as easily score a cheap flight this winter, where the park is open with only slight operational changes as well as distancing rules in place. From Chicago (ORD), we were able to find February flights to Orlando (MCO) for $127 round-trip, nonstop, on American. Meanwhile, from Seattle (SEA), a February nonstop to Ft. Lauderdale is just $197 round-trip on Alaska. 

Have a look at recent finds from your city to Orlando (MCO), Miami (MIA), Ft. Lauderdale (FLL), and West Palm Beach (PBB).

Flights to Lisbon (LIS), Portugal 

Lisbon, Portugal skyline with Sao Jorge Castle
TTstudio | Adobe Stock

If you’re skittish on both the expense and safety of travel to Europe this winter, Portugal may quash your concerns on all counts. As the country with Europe’s second-highest rate of vaccination after Malta, Portugal is also one of the most affordable destinations on the continent. TAP Portugal, its flag carrier, has some of the lowest fares across the Atlantic and, once there, food and accommodation are much lower than what you’ll find next door in Spain. The only catch? Hotels and homestays tend to fill up fast with Northern Europeans escaping winter at home, so it’s wise to book your lodgings as early as you can. Searching from San Francisco, we found January flights for just $390 round-trip on United, with nonstops on TAP going for $461 round-trip. Meanwhile, from Dallas (DFW), we spotted seats for $556 round-trip on United. 

Check out our current flights to Lisbon (LIS) from your nearby airport. 

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